As evidenced this past week, Kevin Cheveldayoff and the Winnipeg Jets do not only just have a long Summer on their phones (be it desk or cell, if they choose to go to the cottage), but also the next couple of Summers as well. Numerous players are heading to Free Agency, and according to Matt Cane’s 2018 Free Agent Predictions, they may not be cheap depending on the term.

That being said, it is not impossible to manoeuvre cautiously and meticulously to try and keep the core of the team together, while constantly supplanting lost players to free agency with younger, talented prospects. This is, of course, not unlike Stanley Cup Champions of the past – the Washington Capitals (finally) won it all when expectations were lowered due to their reliance on talent within the system; Pittsburgh Penguins won back-to-back with the likes of Guentzel, Rust, Sheary, and most importantly Murray contributing significantly; Teuvo Teravainen and Brandon Saad on their entry-level contracts helped support the core of the Chicago Blackhawks to (arguably) establish the first cap era dynasty.

Does this mean letting some players go via trade or free agency when they are hitting their stride? Possibly. In doing that, does it mean there are no other players available to take their places? 217 overall picks in every NHL Draft suggests otherwise. Add on that the Winnipeg Jets seem to have a fantastic scouting staff and have key risers that could be contributing on the big team sooner than later, and suddenly you feel less panicked and worried about how the Jets can continue competing for the Stanley Cup.

That being said, there is a need to take this one step and one season and off-season at a time, monitoring every little bit of development and changes internally and externally of the Hockey Club and the NHL. So, let us begin with taking another look at what the Jets contracts are currently:

As it currently stands, the Winnipeg Jets have 9 current players on the team heading to Restricted Free Agency, with an additional 4 going to Unrestricted Free Agency. In what is surprising on second glance, with the extreme likelihood that Enstrom is not returning to the Jets (and possibly the NHL), the Jets have an extreme advantage in the sense that they will not need to compete with other teams to retain the core, for now. The difficulty is, however, that some of these RFA negotiations can be long and heavy in negotiations and back-and-forths, leaving much up in the air and trying to figure out which domino falls before the other.

For my analysis, using the previous three articles as a base, I will go in order of importance for signings, why I believe them to be either optimal or hopeful or realistic, and how it can help the Jets in their signings after.

The Vezina-nominee turned many heads this season when he took advantage of an injury-plagued season for the supposed number one, Steve Mason, and now goes into the Summer as probably one of Chevy’s most crucial signings in his tenure here, that will either be praised or criticized for years to come. Matt Cane’s model believes that Hellebuyck is worth a lot more than many suspect at $6.7m at either 4 or 5 years, so it will take some crucial negotiating by the Jets’ GMs to use previous comparables to bring the goalie’s ask down.

The most notable comparison and comparable, in my opinion, is none other than recent Stanley Cup Champion, Braden Holtby of the Washington Capitals. At the same age of 25, after signing a short and cheap “prove-it” contract and just being outside of the final Vezina nominees at #4, Holtby signed for 5 years at $6.1m, and the Caps have certainly not regretted it as he continues to put up stellar numbers, especially in the post-season. Arguably, Hellebuyck has not proven as much as Holtby has, especially in one post-season in comparison to Holtby’s three at the time (in which Holtby has been equal or better than Hellebuyck’s .922 SV%), so thus he should not be paid more than him (right?).

That being said, Hellebuyck has that history of being the solid goaltender he was in the past, so a signing of an average annual value of $6,200,000 for 5 years should be well in the ballpark for both parties. It would be disappointing if the Jets had no choice but to sign him to less term; if Hellebuyck opts for arbitration and it goes down that path, there is no doubt Cheveldayoff would choose a term of 1-year in order to keep Hellebuyck’s RFA rights for one more Summer – however, it comes at a cost that if he puts up a similar or close season, that price tag gets significantly more expensive.

In the perspectives of many fans, the Jets have a plethora of right-handed defencemen, and with the scales tipping in favour of Jacob Trouba potentially signing long term, there is simply no room for any NHL team to have three players on one side of their defence take up a significant portion of their payroll. Though the departure of Toby Enstrom does free up room for it to last for one more season for a potential “self-rental” (stealing that one from the Toronto Maples Leafs vocabulary), freeing up the payroll now and gaining assets (particularly of the entry-level contract nature) are crucial for the phase that the Winnipeg Jets now find themselves in.

Trading Tyler Myers isn’t so much for freeing up the payroll now, but for setting themselves up for success in the future. The core of a forward corp composed of Scheifele, Laine and Ehlers, along with defensive stalwarts of Trouba and Morrissey, with a backbone of Connor Hellebuyck is going to be very good, but very expensive. This means that the Jets must take the route where they have the ability to insert cheap contracts – primarily those of entry-level contract calibres and those being extended cheaply under RFA statuses – and thus need more of those players. Their current crop of players of that nature include the likes those with the team now (Kyle Connor, Jack Roslovic, Tucker Poolman) and those who could be high contributors in the future (Kristian Vesalainen, Sami Niku, Mason Appleton, Luke Green, Brendan Lemieux, Logan Stanley). Not having a first round pick in the the 2018 NHL Entry Draft, however, does hurt the idea of constantly replacing cheap – but talented – players.

Luckily for the Winnipeg Jets, there are a slew of teams looking for one final defenceman to complete their puzzle, and Myers is a potential candidate to fulfill those needs. Those teams include the likes of the Edmonton Oilers and the Toronto Maple Leafs, but other potential teams could include the Florida Panthers, Tampa Bay Lightning, and even the Vegas Golden Knights. The two Canadian teams are the most likely candidates: both Toronto and Edmonton appears to have a wealth of non-roster players eager to make the jump now – Toronto needing one final piece to become a contender, and Edmonton needing a key figure and anchor on the defence (though it might take some more manoeuvring on their part to make it happen). Both these teams may be willing to part with a first round draft pick, if not this year then perhaps in the future (if they believe they will be locks for playoffs, resulting in picks in the 20s), which would help the Jets utilize their skill in scouting to bring in the young and cheap talent now needed to carry the core of the team to the ultimate goal of the Stanley Cup.

With Tyler Myers potentially in his final season with the Jets (or traded, as mentioned above), Jacob Trouba becomes all the more important to sign long term and become the keystone player he believes himself to be. When healthy, Trouba provides production on offence, is a stalwart against the top opposition, and eats up significant time-on-ice. As such, you do not want to play any more games in terms of contract negotiations – and by the sounds of rumours, neither does he.

Though Matt Cane’s projections do not see Trouba hitting the $6m mark even when signed to a maximum of 8 years, buying UFA years and paying the “Winnipeg tax” might be what it takes to make this contract negotiation go by swiftly. The defenceman will likely look at the likes of Dustin Byfuglien, Brent Burns, Marc-Édouard Vlasic, Kevin Shattenkirk, and more defenceman who got paid even more money around the age of 30 at the expiry of their second or third contracts, and will likely prefer the short-mid term length. This could play well into Chevy’s side of the negotiations by keeping the upper limit of any contract Trouba signs at $6m, and even getting for less – but do you take the chances of having Trouba’s contract expire around the same time of the likes of Scheifele, Ehlers, and (probably) Hellebuyck?

By forcing a two-year agreement last year, Trouba has forced himself into comparables of those before him: primarily, the likes of Parayko, Rielly, and Slavin. All three of those players got no where close to $6m, with Parayko’s being the highest at 5 years at $5m. The only recent defenceman in memory that has gone more than $6m at around the same age of 25 is Cam Fowler and Victor Hedman – Trouba comes no where close to Hedman’s contributions, and Cam Fowler’s $6.5m came at signing for 8 years. Putting all of this together, signing Trouba at 6 years for $6,000,000 AAV makes too much sense for all parties.

Let us begin by saying that while Laine may not contribute the same as centres do, there simply is no ignoring his contribution to one of the most crucial things in the sport of hockey: goals. Simply put, the recently turned 20-year-old is already scoring at a torrid pace for two seasons in a row, and there is still much, much room to grow, both physically and mentally. In this author’s perspective, it would be a mistake to think that another season of high-scoring but perhaps questionable metrics and defensive play would decrease Laine’s next contract – because if the latter does improve even slightly, the young Finn will undoubtedly be asking for upwards of $10m in his first offseason as a RFA.

For the record, dating back to the off-season of 2013, of the 17 players to receive contracts upwards of 6 years in length and a $7.5m cap hit, around 6 of those players can be considered pure wingers (Benn, Voracek, Tarasenko, Kane, Giroux, Perry):

So, not many wingers get paid close to the $10m mark, unless you are Jamie Benn or Patrick Kane, and are about to hit unrestricted free agency. There’s just one caveat that is sure to be pointed out during contract negotiations starting this July 1st – the following is a top 15 of seasons since 2013-14 of all the players above, ordered by goals:

In about ~100 seasons worth, Laine already has two seasons in the top 15, and has a season that is second amongst those players. Yes, it’s a lot of bucketing going on there, but the point is to stress that Patrik Laine is a pure goal-scorer already – if Jets’ Management waits until Summer 2019 and Laine rounds out the rest of his game by then (and other comparables such as Matthews and others sign by then), Laine is certainly going to be one of those few wingers getting paid close to $10m.

Therefore, Chevy and company need to bite the bullet now and sign Laine for “cheap” – which ideally, is lower than the likes of McDavid and Eichel, yet higher than Draisaitl. There is something to be said about being the second winger ever to get $10m or more, which might be yet another accolade in the story of Patrik Laine – but that is something he can certainly rise up to in his second standard contract at the age of 28, when most of these other players are receiving these expensive contracts. For now, the Jets should make it a prime goal to sign Laine this offseason before it gets significantly harder and more expensive. Though it is merely a guess at this point, I believe that 8 years at $9.25m is the Jets best offer to keep Laine during his prime years here, while allowing for some space for other important players later.

In what might be an overpayment if Lowry’s body does not keep up with his style of play, signing the key role shutdown centre in Paul Maurice’s game plans to a mid-length deal will be important to get as much use out of him as possible is important. It is incredibly likely that the close he approaches his 30s, Adam Lowry won’t contribute as effectively as he is currently – even though this is the most productive (half-)season he had – and thus, you want to definitely keep him for his prime years, and as cheaply as possible, and reevaluate whether or not he is continuing at the same pace or deteriorating going into his 30s.

This is probably one of the most accurate predictions from Matt Cane’s model, though he gives a stronger probability to the edge to a 2 or 3 year deal at around $1.75m to $2.5m. It’s certainly one of the more dramatic predictions, jumping nearly $500k per year depending on the length – but that is the cost of buying years where Lowry could be an unrestricted free agent. If the 25-year-old were to sign a 1-year deal, he would remain a RFA with the Jets for one more off-season. This may sound advantageous to the Jets, but it isn’t the next year where the Jets are going to encounter the most cap crunch, it is the years after in which Laine’s likely long-term and high-costing extension kicks in (and maybe Wheeler’s, too?).

In planning around this, you want to buy only a short amount of Lowry’s UFA years, and likely supplant him with younger talent from the draft at a later point in time. Going for five years is too expensive at a supposed $3.75m; going for two years might be two short, though it comes at a cheaper cost of $1.75m. 4 years at $3.25m helps keep Lowry’s physical presence on the Jets as something to be feared for years to come, before the risk of injury or a decline in play becomes a key part of signing Adam Lowry in the future.

Though Matt Cane projects a two year deal to be the least likely for Josh Morrissey’s first contract after his entry-level (which slid for two years), the Jets will likely consider this the most ideal option for the RFA who does not have any arbitration rights. This gives the team the time to figure out other key signings and potentially extensions in Summer 2019 – particularly of note, Kyle Connor, Blake Wheeler, and Patrik Laine (if he is not resolved by then).

While it certainly would be ideal to go long term already with Morrissey, the most likely option in that avenue is signing him to 5 years. This takes him to age 28, and as seen before when discussing Trouba, the cap hits and lengths there become much more extreme – especially if it gets to the point of competing against other teams in Free Agency. The left-handed defenceman is the most likely candidate this Summer to be bridged as a result, where the Jets can circle back and pay him more appropriately when the likes of Dmitry Kulikov has his contract expiring, and perhaps a decision to be made when it comes to Dustin Byfuglien’s final year of contract.

It certainly wasn’t likely planned to have Trouba and Morrissey become a RFA at the same time, after having to be forced to sign Kulikov last year to shore up the defence and provide some cover if Enstrom were to not return to the Jets (which is what happened), but going down this path means having to take some risks now. Morrissey is unfortunately a prime candidate to explode offensively if he were to get time on the power play – and if Myers is not here for this upcoming season (which I once again, strongly recommend to recoup some assets), he will definitely get that time and draw on his experience and time quarterbacking the power play in the WHL. Or, maybe he only improves his point production slightly – in which you can get Morrissey for longer at the same cost as a Kulikov or Enstrom. Until then, having Morrissey for 2 years at $2.7m is needed to be able to manage the cap in the immediate future while maintaining the core.

With so many players to get through, I wanted to cover the aforementioned six players above, as there is no doubt they are instrumental to the Jets success over a 82-game season and in attempts to get 16 wins in the post-season. The following players I will spend less time on, but make no mistake – surrounding your elite talent with an important supporting cast is crucial to success in today’s NHL. Should they not be re-signed or extended, however, there is the possibility of going to free agency or dipping into the prospect depths in order to continue competing for the Stanley Cup.

As mentioned in the first post, Armia hasn’t solidified his game in the NHL, as he has shown flashes of brilliance but also absolute duds of games. That being said, he is still an important part of the Winnipeg Jets, primarily shorthanded and in controlling play along with the likes of Lowry and Tanev. All that considered – he isn’t a make or break player on the Jets squad. Armia may likely be asked to sign a 1-year contract in order for the Jets to still retain RFA rights, but the Jets may look to plan for the expansion draft by signing him for 2-years at a cheap cost and make him easy fodder for the (likely) new team in Seattle. Following Cane’s projections (but slightly lower), Armia comes in at 2 years at $1.65m.

What do you pay a player who had one of the most surprising hat tricks ever this past season, and has shown the same hustle in that game in every game he plays? Unfortunately for Tanev, it does not really amount to much when that was half of his year’s production in one game, and it is unlikely he is ever to repeat it. Still, the Jets management is likely enthused that Tanev of 2017-18 was not the same Tanev of 2016-17, and should offer him a slight bump in pay because of it. Since this is Tanev’s last offseason as a RFA, the Jets may opt to buy one UFA year, which is why I believe he will be a tad more expensive the Cane’s prediction of $765k. Still, 2 years at $925k for a player that will never stop hustling and should hopefully be sure to keep surprising, and doesn’t inhibit any the Jets future moves in managing the cap should be worthwhile.

I’ll admit, this one is a bit more of a guess considering that Matt Cane did not include the short amount of Poolman’s games played for his analysis, but there is no doubt that the Jets value Poolman highly. Should Myers be traded, the Jets will likely want to see Poolman regularly on the third-pairing, and now at age 25, it would be a waste to stifle his potential any longer with the Moose. Having Poolman available and ready right now to take significant ice time is one of the main reasons why it is so easy to advocate trading Tyler Myers; and clearly the Jets feel the same way considering he was always just one injury away from playing and even had two games in the Stanley Cup Playoffs. Signing him to 1-year at $1.2m keeps Poolman as a RFA for one more offseason to truly evaluate his worth, and it is possible to slightly overpay him now with the likes of Enstrom and Matthias coming off the payroll (and possibly Myers being traded away).

Still a bit of a far cry from the playoff beast he was back with the Boston Bruins, Joe Morrow does appear to have the tool set to be an effective press box defenceman in the NHL. In comparison to some other player on the team that I’ll suggest something else for, he is both young and can have his rights controlled for one more year should he only sign a one-year deal. He did come in admirably for the Jets this post-season when Enstrom was not ready to return in the first round, and does have the skills that are more effective for the team and today’s NHL in comparison to just hitting people and putting one’s self out of position. Though it’ll take him into UFA status, signing Morrow at 2 years for $800k should put some stability on the left-side of the ice along with Kulikov, Morrisey, and Niku(!) in case of injury.

When looking at another team in the central division that has been considered a contender, I am always surprised at some of the frugal signings that David Poile and the Nashville Predators have managed to get. The one that stands out to me the most is Calle Jarnkrok, signed at 6 years for $2m per year, and has put up 30+ points each for the past three seasons and a multitool in Laviolette’s lineup. I think this should be mimicked for Andrew Copp of the Winnipeg Jets, who can be an effective 4th line centre, or slide up as a winger utilizing his fast speed and forechecking prowess. Should the Jets be able to sign an effective multi-use player like Copp for this low cost extension of 4 years at $1.8m, the Jets will be able to worry about one less player that can be versatile no matter where he is in the lineup and what role he plays.

Let’s be serious – he probably won’t actually see the ice at all, but the Jets do need an effective player ready to go in the press box. Dano will probably continue to be that guy.

At the age of 20 in his first professional season playing on North American ice, the 7th round draft pick absolutely crushed the competition and received numerous accolades as a result. While it is only one season, as mentioned before, the Jets need to start utilizing even more of their younger talent (again), and Sami Niku is a prime candidate to be an effective third-pairing with the likes of Tucker Poolman. Morrow and Chiarot are good as insurance, but are what they are – Niku brings in more dynamic talent, further speeds up the game, and can be utilized both on the power play and penalty kill if needed. Niku can also come into this season somewhat sheltered on the third pairing and find friendship and encouragement with his fellow Finns, Armia and Laine (and soon to be Vesalainen). In this author’s opinion, bringing in Niku not only replaces the loss of Enstrom and Myers; he singlehandedly can perform to both of their strengths and continue to learn and grow in the NHL game.

Roslovic has shown in limited games with talented teammates that he can contribute at a high level already in the NHL. While it perhaps would have been ideal to have him in the AHL for the majority of the previous season to work on his game as a centre, his time as a winger with the likes of Perreault and Little in the NHL has shown that the young American has the talent already to produce offence. By working him in slowly over the season as a centre, perhaps giving him some familiarity and a veteran winger with the likes of Kyle Connor and Matheu Perreault will be crucial in helping Roslovic become the talented centre the Jets organization believe him to be when they originally drafted him.

Ben Chiarot brings in one element on defence: physicality in hits. However, his poor gap control in preventing controlled entries, panic in exiting his defensive zone when pressured, and lack of creating controlled entries for his own team’s offence, is too much problems for a player earning $1.4m. According to the CBA, $1.025m of that can be buried in the AHL, should Chiarot not be claimed on waivers. When Morrow can be had for cheaper, and Niku can be brought in to be the third pairing on the Jets, Chiarot is expendable. If he is claimed on waivers, all the better – it just simply means that the Jets need to help out the Moose a little bit more with signings for their squad.

Should the Jets be able to have successful contract negotiations this Summer 2018 and hit close to the mark on my predictions, the ending result will look like this. With the cap supposedly going up to $80m this year, the Jets will need to leave themselves open enough for bonuses so they do not get penalized for any overages. As such, they will need to be prepared to have a buffer of around $3.9m should all of Laine, Connor, Roslovic, and hopefully Niku all max out their bonuses. With the 1- and 2-year signings of Armia, Tanev, Morrissey, Poolman, and Morrow, they are well equipped to manage that, while more importantly paying the likes of Laine, Lowry, Trouba, and Hellebuyck a reasonable amount of money – of course, banking on the fact that Myers is traded to free up the $5.5m cap hit he carries.

Most importantly to this plan is the freedom to sign important players in Summer 2019 for the 2019-20 season. Wheeler is undoubtedly worth more than the $5.6m he is currently getting paid, and likewise Kyle Connor for his contract coming out of his entry-level. With Steve Mason and Mark Stuart’s buyout coming off the books, it frees up another close to $4.7m to go towards those players – though likely, the Jets management at that time may pay ~$1.5m for a reliable backup goaltender to Connor Hellebuyck, so really there’s an additional $3.2m. Divvy that up by giving Wheeler the freed up $2.6m (contract at $7.2m) and bridge Connor with the remaining $1.8m (contract at $2.7m), and you can continue to keep the current Jets core together for the foreseeable future.

Is it all optimistic and pointless rambling? Of course. But the point of these articles were not to feed a fever dream of how to keep the 2017-18 Western Conference Finalists together (okay, maybe it was); but rather, to point out how the Jets have key decisions to make this Summer that will make or break their chances at a Stanley Cup for years to come.

It isn’t an enviable position to be in, and rather than me typing out words and cross-referencing several sources of data and analysis, Kevin Cheveldayoff and company will be holding countless conversations and negotiations with agents and players alike, everybody trying to compete for their piece of the pie. Whatever those decisions end up being, this one fan is eager to see what incarnation of the Winnipeg Jets we will see come 2018-19.

But, I think this is the most optimal.